Potassium Iodide → [2-(2-propynyloxy)phenyl]methanol

HRID 654329Notes

Reaction equation

HRID 654329 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]#[CH:19].[I-].[K+]>C(C(C)=O)C.C1(C)C=CC=CC=1>[CH2:19]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][OH:1])[C:18]#[CH:17]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 5146Salicyl AlcoholHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 2764526[2-(2-propynyloxy)phenyl]methanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 2-(hydroxymethyl)phenol (10.0 g, 80.6 mmol) slurried in 300 ml of methyl ethyl ketone was added 1.2 equivalents of potassium carbonate. Then 3-bromopropyne (121 mmol, 18 g of an 80% solution in toluene) and potassium iodide (0.5 g) were added and the reaction was refluxed overnight. After cooling the salts were filtered off. The filtrate was concentrated and the residue was dissolved in water and extracted twice with ether. After washing with water and brine, the organic layer was dried over MgSO4 and concentrated to afford the subtitle compound.

Workup

  1. temperaturethe reaction was refluxed overnight
  2. temperatureAfter cooling the salts
  3. filtrationwere filtered off
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in water
  6. extractionextracted twice with ether
  7. washAfter washing with water and brine
  8. dry with materialthe organic layer was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e1dcf337c63e4066a95107e99e746e9b
Source dataset
uspto-grants-1992_07
Patent number
US05130485

Reaction notes

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